Habits must evolve with life's seasons (e.g., career changes, having children). A habit that served you well in one phase may hold you back in the next. Be willing to give up old, successful routines that no longer align with your current priorities and identity.

In an era of accelerating change, a manager's role is to be like a willow tree. They must provide a sturdy, stable vision for the team while remaining highly flexible in how they adapt to storms and changing conditions. This combination builds team resilience.

Barry Diller's key lesson from failure is that experience breeds cynicism, which corrupts good decision-making. He advises leaders to constantly fight this tendency and "scrub their instincts clean." Maintaining a degree of naivete is crucial for accurately judging new ideas without being biased by past negative experiences.

Traits like extreme responsiveness, which earn praise early in a career, can lead to burnout and poor prioritization at senior levels. Leaders must recognize when a once-beneficial belief no longer serves their new, scaled responsibilities and becomes a limiting factor.

The pace of change in AI means even senior leaders must adopt a learner's mindset. Humility is teachability, and teachability is survivability. Successful leaders are willing to learn from junior colleagues, take basic courses, and admit they don't know everything, which is crucial when there is no established blueprint.

Bruce Lee’s philosophy to be “formless, shapeless, like water” is a powerful model for investors. It warns against rigid adherence to a single dogma, like old-school value investing, and instead encourages adapting one's strategy to fit the unique conditions of the current market environment.

People have an extreme aversion to acute pain. They will accept any level of chronic pain—like a company slowly bleeding out over five years—to avoid the single, difficult conversation or dramatic change required to stop the losing. This explains the long, slow death of many companies.

While experience builds valuable pattern recognition, relying on old mental models in a rapidly changing environment can be a significant flaw. Wise leaders must balance their experience with the humility and curiosity to listen to younger team members who may have a more current and accurate understanding of the world.

Contrary to the stereotype of being 'dusty' or resistant to change, companies that last for centuries are masters of adaptation. Their longevity is direct evidence of their forward-thinking ability to navigate crises, from wars and pandemics to technological disruption.